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Details

Stereochemistry ACHIRAL
Molecular Formula C13H14N6O
Molecular Weight 270.2899
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VOXTALISIB

SMILES

CCN1C(=O)C(=CC2=C(C)N=C(N)N=C12)C3=CC=NN3

InChI

InChIKey=RGHYDLZMTYDBDT-UHFFFAOYSA-N
InChI=1S/C13H14N6O/c1-3-19-11-8(7(2)16-13(14)17-11)6-9(12(19)20)10-4-5-15-18-10/h4-6H,3H2,1-2H3,(H,15,18)(H2,14,16,17)

HIDE SMILES / InChI

Molecular Formula C13H14N6O
Molecular Weight 270.2899
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Voxtalisib (SAR245409, XL765) is an orally available inhibitor of PI3K and the mammalian target of rapamycin (mTOR), which are frequently activated in human tumors and play central roles in tumor cell proliferation. Exelixis discovered Voxtalisib internally and out-licensed the compound to Sanofi. Voxtalisib is being evaluated by Sanofi as a single agent and in multiple combination regimens in a variety of cancer indications. Clinical trials have included a single agent phase 2 trial in Non-Hodgkin’s lymphoma, combination phase 1b/2 trials with temozolomide in patients with glioblastoma, with letrozole in hormone receptor positive breast cancer, with bendamustine and/or rituximab in lymphoma or leukemia, and a phase 1 trial in combination with a MEK inhibitor. Voxtalisib is a highly selective, potent and reversible ATP-competitive inhibitor of pan-Class I PI3K (α, β, γ, and δ) and mTORC1/mTORC2. It is orally active, highly selective over 130 other protein kinases. In cellular assays, XL765 inhibits the formation of PIP3 in the membrane, and inhibits phosphorylation of AKT, p70S6K, and S6 phosphorylation in multiple tumor cell lines with different genetic alterations affecting the PI3K pathway.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Drug discovery approaches targeting the PI3K/Akt pathway in cancer.
2008 Sep 18
Characterization of the activity of the PI3K/mTOR inhibitor XL765 (SAR245409) in tumor models with diverse genetic alterations affecting the PI3K pathway.
2014 May
Patents

Sample Use Guides

In Vivo Use Guide
50 mg twice daily: no eating for 2 hours prior and 1 hour after dose
Route of Administration: Oral
In Vitro Use Guide
Voxtalisib treatment results in decreased cell viability in 13 PDA cell lines in a dose-dependent manner. 10uM induced approx. 40% apoptosis in BxPC-3 cells.
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:15:39 UTC 2019
Edited
by admin
on Mon Oct 21 23:15:39 UTC 2019
Record UNII
CVL1685GPH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VOXTALISIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
SAR-245409
Code English
SAR245409
Code English
PYRIDO(2,3-D)PYRIMIDIN-7(8H)-ONE, 2-AMINO-8-ETHYL-4-METHYL-6-(1H-PYRAZOL-3-YL)-
Systematic Name English
XL-765
Code English
2-AMINO-8-ETHYL-4-METHYL-6-(1H-PYRAZOL-3-YL)PYRIDO(2,3-D)PYRIMIDIN-
Systematic Name English
2-AMINO-8-ETHYL-4-METHYL-6-(1H-PYRAZOL-5-YL)PYRIDO(2,3-D)PYRIMIDIN-7(8H)-ONE
Systematic Name English
VOXTALISIB [INN]
Common Name English
VOXTALISIB [USAN]
Common Name English
XL765
Code English
VOXTALISIB [WHO-DD]
Common Name English
2-AMINO-8-ETHYL-4-METHYL-6-(1H-PYRAZOL-3-YL)PYRIDO(2,3-D)PYRIMIDIN-7(8H)-ONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
NCI_THESAURUS C2152
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
Code System Code Type Description
EVMPD
SUB184196
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
PRIMARY
NCI_THESAURUS
C71704
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
PRIMARY
PUBCHEM
16123056
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
PRIMARY
CAS
934493-76-2
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
PRIMARY
ChEMBL
CHEMBL3545366
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
PRIMARY
INN
9709
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
PRIMARY
CAS
1123889-87-1
Created by admin on Mon Oct 21 23:15:39 UTC 2019 , Edited by admin on Mon Oct 21 23:15:39 UTC 2019
SUPERSEDED
Related Record Type Details
ACTIVE MOIETY